Here’s a weird one. I recently started using a VPN on my Plex server. If I turn off my wifi on my Pixel 3a and try to connect to my Plex server via the Plexamp app it just spins and never loads. BUT if I open the Plex app on my phone that DOES connect. And after that connects I can go back into Plexamp and then I see I am connected there as well and everything works perfectly.
So I can connect to my Plex server behind a VPN via Plexamp but ONLY if I open the Plex app on my phone and let it connect there first. Weird huh? Any ideas?